Stereocontrolled 1,2- Glycosylation As the Driving Force of Progress in Synthetic Carbohydrate Chemistry

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2015 Jun 17

PMID 26078847

Citations 99

Authors

Swati S Nigudkar

Alexei V Demchenko

Affiliations

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References

Fascione M, Adshead S, Stalford S, Kilner C, Leach A, Turnbull W . Stereoselective glycosylation using oxathiane glycosyl donors. Chem Commun (Camb). 2009; (39):5841-3. DOI: 10.1039/b913308a. View

Kochetkov N, Klimov E, Malysheva N, Demchenko A . A new stereospecific method for 1,2-cis-glycosylation. Carbohydr Res. 1991; 212:77-91. DOI: 10.1016/0008-6215(91)84047-i. View

Yin Z, Huang X . Recent Development in Carbohydrate Based Anti-cancer Vaccines. J Carbohydr Chem. 2012; 31(3):143-186. PMC: 3312792. DOI: 10.1080/07328303.2012.659364. View

Baek J, Lee B, Jo M, Kim K . Beta-directing effect of electron-withdrawing groups at O-3, O-4, and O-6 positions and alpha-directing effect by remote participation of 3-O-acyl and 6-O-acetyl groups of donors in mannopyranosylations. J Am Chem Soc. 2009; 131(48):17705-13. DOI: 10.1021/ja907252u. View

Crich D, Smith M . S-(4-methoxyphenyl) benzenethiosulfinate (MPBT)/trifluoromethanesulfonic anhydride: a convenient system for the generation of glycosyl triflates from thioglycosides. Org Lett. 2000; 2(25):4067-9. DOI: 10.1021/ol006715o. View

Ruei J, Venukumar P, Ingle A, Mong K . C6 picoloyl protection: a remote stereodirecting group for 2-deoxy-β-glycoside formation. Chem Commun (Camb). 2014; 51(25):5394-7. DOI: 10.1039/c4cc08465a. View

Robbins J, Lee C, Rastogi S, Schiffman G, HENRICHSEN J . Comparative immunogenicity of group 6 pneumococcal type 6A(6) and type 6B(26) capsular polysaccharides. Infect Immun. 1979; 26(3):1116-22. PMC: 414736. DOI: 10.1128/iai.26.3.1116-1122.1979. View

Mensah E, Azzarelli J, Nguyen H . Palladium-controlled beta-selective glycosylation in the absence of the C(2)-ester participatory group. J Org Chem. 2009; 74(4):1650-7. DOI: 10.1021/jo802468p. View

Lopes L, da Silva M, Bittencourt V, Figueiredo R, Rollin-Pinheiro R, Sassaki G . Glycoconjugates and polysaccharides from the Scedosporium/Pseudallescheria boydii complex: structural characterisation, involvement in cell differentiation, cell recognition and virulence. Mycoses. 2011; 54 Suppl 3:28-36. DOI: 10.1111/j.1439-0507.2011.02105.x. View

10.

Meng B, Zhu Z, Baker D . 1,2-cis Alkyl glycosides: straightforward glycosylation from unprotected 1-thioglycosyl donors. Org Biomol Chem. 2014; 12(28):5182-91. DOI: 10.1039/c4ob00626g. View

11.

Balmond E, Coe D, Galan M, McGarrigle E . α-Selective organocatalytic synthesis of 2-deoxygalactosides. Angew Chem Int Ed Engl. 2012; 51(36):9152-5. DOI: 10.1002/anie.201204505. View

12.

Zhao C, Li M, Luo Y, Wu W . Isolation and structural characterization of an immunostimulating polysaccharide from fuzi, Aconitum carmichaeli. Carbohydr Res. 2006; 341(4):485-91. DOI: 10.1016/j.carres.2005.11.032. View

13.

Rencurosi A, Lay L, Russo G, Caneva E, Poletti L . NMR evidence for the participation of triflated ionic liquids in glycosylation reaction mechanisms. Carbohydr Res. 2006; 341(7):903-8. DOI: 10.1016/j.carres.2006.02.021. View

14.

Boltje T, Kim J, Park J, Boons G . Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched alpha-glucan. Nat Chem. 2010; 2(7):552-7. PMC: 2892400. DOI: 10.1038/nchem.663. View

15.

Liu L, Pohl N . A fluorous phosphate protecting group with applications to carbohydrate synthesis. Org Lett. 2011; 13(7):1824-7. PMC: 3127408. DOI: 10.1021/ol2003435. View

16.

Crich D, Jayalath P . Stereocontrolled formation of beta-glucosides and related linkages in the absence of neighboring group participation: influence of a trans-fused 2,3-O-carbonate group. J Org Chem. 2005; 70(18):7252-9. DOI: 10.1021/jo0508999. View

17.

Codee J, Hossain L, Seeberger P . Efficient installation of beta-mannosides using a dehydrative coupling strategy. Org Lett. 2005; 7(15):3251-4. DOI: 10.1021/ol051038p. View

18.

Babu R, Zhou M, ODoherty G . De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction. J Am Chem Soc. 2004; 126(11):3428-9. DOI: 10.1021/ja039400n. View

19.

Guo H, ODoherty G . De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide. J Org Chem. 2008; 73(14):5211-20. DOI: 10.1021/jo800691v. View

20.

Ohtake H, Ichiba N, Ikegami S . A highly stereoselective construction of beta-glycosyl linkages by reductive cleavage of cyclic sugar ortho esters. J Org Chem. 2000; 65(24):8171-9. DOI: 10.1021/jo0005870. View